Strategy & Operations Senior Associate

About Clipboard

Clipboard's mission is to uplift communities through an app-based marketplace connecting healthcare professionals with workplaces that need qualified workers. Founded in 2016, Clipboard is a remote-first team of over 1,000 people, a top Y-Combinator company, and has been profitable since 2022. We are the leader in Long-Term Care staffing and rapidly expanding into Home Health, Hospitals, and beyond.

About This Role

The Strategy & Operations Senior Associate is an experienced generalist role suited for versatile problem-solvers who thrive across multiple domains. You are resourceful, adaptable, and confident in your ability to tackle diverse challenges. Your initial focus will be on the Billing team, with project scope determined by your strengths and organizational needs.

Example Initiatives

• Build internal predictive analytics models and underwriting processes to identify high-risk payers early and inform contracting and risk mitigation decisions
• Research, evaluate, and onboard vendors offering AI-powered collections solutions for customer-facing efforts
• Redesign payment conversion processes to accelerate cash flow (e.g., migrating cheque payments to eCheck)
• Lead and manage teams of Billing Account Managers

Billing Team Context

Clipboard operates as a capital-intensive, lending-like business: we pay healthcare professionals immediately after shifts, then collect payment from workplaces 30+ days later. The Billing team maximizes profitability by accelerating collections, minimizing losses, and preserving customer experience—directly supporting reliable revenue-to-cash conversion and high-quality growth.

What We're Looking For

You:

• Are an experienced generalist comfortable solving multiple problem types
• Demonstrate resourcefulness and adaptability in dynamic environments
• Excel at deep problem investigation and creative solution design
• Thrive in remote-first, collaborative settings

Salary Disclosure: This is an editorial market estimate of $80K–$130K USD annually, based on role level and market data. This is not employer-provided compensation and may vary significantly by experience, location, and performance.